CN113166311B - Composition for optical material and optical material - Google Patents

Abstract

The present invention provides a composition for optical materials, and an optical material containing the same, characterized in that the composition for optical materials contains (A) 100 parts by mass of a polymerizable monomer, and (B) a maximum absorption wavelength It is 0.001-0.3 mass parts of the ultraviolet absorber which has a specific structure of 360 nm or more and less than 380 nm. According to the present invention, it is possible to provide a composition for optical materials containing an ultraviolet absorber having good long-term storage stability and an optical material containing the same, especially a composition for optical materials capable of forming a plastic lens with a high blocking rate of blue light. .

Description

Composition for optical material and optical material

technical field

The present invention provides a composition for optical materials containing an ultraviolet absorber having good long-term storage stability and an optical material containing the same, and in particular provides a composition for optical materials capable of forming a plastic lens with a high blocking rate of blue light.

Background technique

The adverse effects of UV exposure to the eyes have long been viewed as a problem. In addition, in recent years, it is said that the energy of light in the blue region (380-500 nm) (hereinafter also referred to as blue light) that is healthy for the eyes is also strong, thereby causing damage to the retina and the like. The damage caused by blue light is called "blue light hazard". In order to prevent such damage, it is said that it is particularly desirable to block short-wavelength blue light around 380 to 420 nm.

In order to solve such a problem, for example, Patent Document 1 proposes a lens provided with a multilayer film disposed on a convex surface of a plastic member, and the multilayer film has an average reflectance of 2 to 10% in the wavelength range of 400 to 500 nm. . However, when the blue light blocking rate of this lens was measured, it was about 30%.

In addition, Patent Documents 2 and 3 describe polymerizable compositions for lenses containing a benzotriazole-based ultraviolet absorber to increase the light blocking rate, but they only focus on absorption below 405 nm, and do not discuss any blue light blocking rate. .

In addition, Patent Documents 4 and 5 propose a polymerizable product for lenses that contains 2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-chlorobenzotriazole ultraviolet absorber and improves the blue light blocking rate. Composition, but the solubility of the UV absorber in the monomer is low, so the long-term storage stability is poor.

prior art literature

patent documents

Patent Document 1: Japanese Patent Laid-Open No. 2012-093689

Patent Document 2: Japanese Patent Laid-Open No. 2008-056854

Patent Document 3: Japanese Patent Laid-Open No. 2010-84006

Patent Document 4: Japanese Patent No. 5620033

Patent Document 5: Japanese Patent No. 6294386

Contents of the invention

The problem to be solved by the invention

Therefore, an object of the present invention is to provide a composition for optical materials and an optical material containing the same having good long-term storage stability, especially to provide a composition for optical materials capable of forming a plastic lens with a high blocking rate against blue light.

means of solving problems

The inventors of the present invention conducted intensive research to achieve the above object, and found that the above object can be achieved by using an ultraviolet absorber containing a benzotriazole compound having a maximum absorption wavelength of 360 nm or more and less than 380 nm. the invention.

That is, the present invention relates to the following:

[1] A composition for optical materials, characterized by containing (A) 100 parts by mass of a polymerizable monomer, and (B) an ultraviolet absorber represented by the following formula (1) having a maximum absorption wavelength of 360 nm or more and less than 380 nm. 0.001 to 0.3 parts by mass.

[chemical 1]

(Wherein, R1 represents a hydrogen atom, an alkyl group with ¹ to 8 carbons, an alkoxy group with 1 to 8 carbons, a hydroxyl group, a linear or branched monosubstituted amino group with 1 to 4 carbons, a single substituted amino group with 1 to 8 carbons, 4 linear or branched disubstituted amino groups, nitro groups, carboxyl groups, alkoxycarbonyl groups with 1 to 8 carbon atoms, hydroxyalkyl groups with 1 to 8 carbon atoms, and alkyl groups with 1 to 8 carbon atoms each Alkylcarbonyloxyalkyl of 8, carboxyalkyl with 1 to 3 carbon atoms in the alkyl group, alkoxycarbonylalkyl group with 2 to 10 carbon atoms in total in the alkyl group, aryl group, acyl group, sulfo group or cyano group base;

R ² represents a hydroxyl group, an alkoxy group with 1 to 8 carbons, an alkylthio group with 1 to 8 carbons, a linear or branched monosubstituted amino group with 1 to 4 carbons, a straight or branched amino group with 1 to 4 carbons branched disubstituted amino;

R ³ represents a hydrogen atom, a hydroxyl group, an alkyl or alkoxy group with 1 to 8 carbons, a straight or branched monosubstituted amino group with 1 to 4 carbons, a straight or branched diatom with 1 to 4 carbons substituted amino,

A ring structure in which R2 and ^R3 are cross ^- linked is also possible. )

The present invention can take the following embodiments.

[2] The composition for an optical material according to the above [1], wherein the polymerizable monomer (A) contains:

selected from bis(isocyanatomethyl)bicyclo[2.2.1]heptane, xylylene diisocyanate, 4,4'-methylene diphenyl diisocyanate, 2,4'-methylene diphenyl At least one polyisocyanate compound of diisocyanate and methyl-1,3-phenylene diisocyanate, and

At least one polythiol compound selected from pentaerythritol tetrakis(3-mercaptopropionate) and 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane.

[3] The composition for an optical material according to the above [1], wherein the polymerizable monomer (A) contains:

bis(2,3-epithiopropyl) disulfide, and

With 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6, A mixture of 9-trithiaundecane and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components.

[4] An optical material comprising a cured product obtained by polymerizing and curing the composition for an optical material according to any one of the above [1] to [3], wherein the light transmittance at a wavelength of 400 nm is 5 % or less and the light transmittance at a wavelength of 420 nm is 70% or less, and the light blocking rate in the wavelength range of 380 to 500 nm is 35% or more.

[5] A plastic lens comprising the optical material described in [4] above.

In the present invention, the measurement of the maximum absorption wavelength and the like of each compound is performed in a solvent that does not affect the measurement. As this solvent, chloroform is mentioned, for example.

Invention effect

By polymerizing and curing the composition for optical materials of the present invention, an optical material with a high blocking rate of blue light, especially a plastic lens containing the optical material, can be obtained. In addition, because the storage stability of the composition is good, its utility value high.

detailed description

The composition for optical materials of the present invention is characterized in that it contains:

(A) 100 parts by mass of a polymerizable monomer, and

(B) 0.001 to 0.3 parts by mass of an ultraviolet absorber having a maximum absorption wavelength of 360 nm to less than 380 nm and having a specific structure.

Hereinafter, each component is demonstrated.

<(A) Component: Polymerizable Monomer>

In the present invention, known polymerizable monomers can be used.

As the polymerizable monomer applicable to the composition for optical materials, known polyaddition-based monomers (hereinafter sometimes simply referred to as "component (A1)"), cationically polymerizable monomers (hereinafter sometimes simply referred to as "component (A1)"), (A2) component") and a radically polymerizable monomer (it may only be called "(A3) component" hereafter).

<(A1) Addition polymerizable monomer>

The polyaddition-based polymerizable monomer of the present invention can use known monomers without particular limitation, for example: as a monomer for obtaining polyurethane resin, polythiourethane resin, polyurea resin, polyurethane-polyurea resin, polythioammonium Monomers used as raw materials for resins such as ester-polyurea resins. Specifically, it can be used in the form of the following combinations: a combination of polyisocyanate compound and polyol compound; a combination of polyisocyanate compound and polythiol compound; a combination of polyisocyanate compound and polyamine compound; polyisocyanate compound, polyol compound Combination of compound and polyamine compound; combination of polyisocyanate compound, polythiol compound and polyamine compound, the combination of these monomers can be used alone or in combination.

Hereinafter, the polyaddition type polymerizable monomer will be described in detail.

<(A1-1) Polyisocyanate compound>

The polyisocyanate compound (hereinafter sometimes simply referred to as component (A1-1)) is not particularly limited, but specific examples thereof include bis(isocyanatomethyl)cyclohexane, bis(isocyanatomethyl) Bicyclo[2.2.1]heptane, hydrogenated 2,6-toluene diisocyanate, hydrogenated m-phenylene diisocyanate, hydrogenated p-phenylene diisocyanate, hydrogenated 2,4-toluene diisocyanate, hydrogenated diphenylmethane diisocyanate, hydrogenated m-phenylene diisocyanate Alicyclic isocyanate compounds such as dimethyl diisocyanate, hydrogenated p-xylylene diisocyanate, and isophorone diisocyanate; phenylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, Aromatic isocyanate compounds such as tetramethylxylylene diisocyanate, 2,6-naphthalene diisocyanate, 1,5-naphthalene diisocyanate; hexamethylene diisocyanate, octamethylene diisocyanate, 2,2,4 - Trimethylhexamethylene diisocyanate, tetramethylene diisocyanate, biuret reaction product of hexamethylene diisocyanate, trimer of hexamethylene diisocyanate, lysine diisocyanate, lysine Acid triisocyanate, 1,6,11-undecane triisocyanate, triphenylmethane triisocyanate and other isocyanate compounds without alicyclic or aromatic rings; diphenyl disulfide-4,4'-diisocyanate, 2 ,2′-Dimethyl diphenyl disulfide-5,5′-diisocyanate, 3,3′-Dimethyl diphenyl disulfide-5,5′-diisocyanate, 3,3′- Dimethyl diphenyl disulfide-6,6'-diisocyanate, 4,4'-dimethyl diphenyl disulfide-5,5'-diisocyanate, 3,3'-dimethoxy Diphenyl disulfide-4,4'-diisocyanate, 4,4'-dimethoxydiphenyl disulfide-3,3'-diisocyanate, diphenyl sulfone-4,4'-di Isocyanate, diphenylsulfone-3,3′-diisocyanate, benzylsulfone-4,4′-diisocyanate, diphenylmethanesulfone-4,4′-diisocyanate, 4-methyldiphenylmethane Sulfone-2,4′-diisocyanate, 4,4′-dimethoxydiphenylsulfone-3,3′-diisocyanate, 3,3′-dimethoxy-4,4′-diisocyanate Acidodibenzylsulfone, 4,4′-dimethyldiphenylsulfone-3,3′-diisocyanate, 4,4′-di-tert-butyldiphenylsulfone-3,3′-diisocyanate, 4,4′-dimethoxystyrene disulfone-3,3′-diisocyanate, 4,4′-dichlorodiphenylsulfone-3,3′-diisocyanate, 4-methyl-3-isocyanate Cyanatobenzenesulfonyl-4′-isocyanatophenolate, 4-methoxy-3-isocyanatobenzenesulfonyl-4′-isocyanatophenolate, 4-methyl-3- Isocyanatobenzenesulfonylanilide-3'-methyl-4'-isocyanate, diphenylsulfonyl-ethylenediamine-4,4'-diisocyanate, 4,4'-dimethoxybenzenesulfonate Acyl-ethylenediamine-3,3′-diisocyanate, 4-methyl-3-isocyanatobenzenesulfonanilide-4-methyl-3′ -isocyanate, thiophene-2,5-diisocyanate, methyl thiophene-2,5-diisocyanate, 1,4-dithiane-2,5-diisocyanate, 1,4-dithiane-2, 5-Diisocyanate methyl ester, 1,4-dithiane-2,3-diisocyanate methyl ester, 1,4-dithiane-2-isocyanatomethyl-5-isocyanate Propyl ester, 1,3-dithiolane-4,5-diisocyanate, 1,3-dithiolane-4,5-diisocyanate methyl ester, 1,3-dithia Cyclopentane-2-methyl-4,5-methyl diisocyanate, 1,3-dithiolane-2,2-ethyl diisocyanate, tetrahydrothiophene-2,5- Diisocyanate, methyl tetrahydrothiophene-2,5-diisocyanate, ethyl tetrahydrothiophene-2,5-diisocyanate, methyl tetrahydrothiophene-3,4-diisocyanate, etc. contain sulfur isocyanate compounds. Among them, alicyclic isocyanate compounds are preferable.

<(A1-2) Polythiol compound>

Examples of the above-mentioned polythiol compound (hereinafter sometimes simply referred to as component (A1-2)) include methanedithiol, 1,2-ethanedithiol, 1,1-propanedithiol, 1,2 -Propanedithiol, 1,3-propaneedithiol, 2,2-propaneedithiol, 1,6-hexaneedithiol, 1,2,3-propanetrithiol, tetrakis(mercaptomethyl) Methane, 1,1-cyclohexanedithiol, 1,2-cyclohexanedithiol, 2,2-dimethylpropane-1,3-dithiol, 3,4-dimethoxybutane- 1,2-dithiol, 2-methylcyclohexane-2,3-dithiol, 1,1-bis(mercaptomethyl)cyclohexane, bis(2-mercaptoethyl) thiomalate , 2,3-dimercaptosuccinic acid (2-mercaptoethyl ester), 2,3-dimercapto-1-propanol (2-mercaptoacetate), 2,3-dimercapto-1-propanol (3 -mercaptoacetate), diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), 1,2-dimercaptopropyl methyl ether, 2,3-di Mercaptopropyl methyl ether, 2,2-bis(mercaptomethyl)-1,3-propanedithiol, bis(2-mercaptoethyl)ether, ethylene glycol bis(2-mercaptoacetate), Ethylene glycol bis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate) ) ester, pentaerythritol tetrakis(3-mercaptopropionate), 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane and other aliphatic mercaptans; 1,2-dimercaptobenzene, 1,3- Dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1, 3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,2-bis(mercaptomethoxy)benzene, 1,3-bis(mercaptomethoxy)benzene, 1, 4-bis(mercaptomethoxy)benzene, 1,2-bis(mercaptoethoxy)benzene, 1,3-bis(mercaptoethoxy)benzene, 1,4-bis(mercaptoethoxy)benzene, 1,2,3-Trimercaptobenzene, 1,2,4-Trimercaptobenzene, 1,3,5-Trimercaptobenzene, 1,2,3-Tris(mercaptomethyl)benzene, 1,2,4- Tris(mercaptomethyl)benzene, 1,3,5-tris(mercaptomethyl)benzene, 1,2,3-tris(mercaptoethyl)benzene, 1,2,4-tris(mercaptoethyl)benzene, 1,3,5-tris(mercaptoethyl)benzene, 1,2,3-tris(mercaptomethoxy)benzene, 1,2,4-tris(mercaptomethoxy)benzene, 1,3,5- Tris(mercaptomethoxy)benzene, 1,2,3-tris(mercaptoethoxy)benzene, 1,2,4-tris(mercaptoethoxy)benzene, 1,3,5-tris(mercaptoethoxy) base) benzene, 1,2,3,4-tetramercaptobenzene, 1,2,3,5-tetramercaptobenzene, 1,2,4,5-tetramercaptobenzene, 1,2,3,4-tetra( Mercaptomethyl) benzene, 1,2,3,5-tetra(mercaptomethyl)benzene, 1,2,4,5-tetra(mercaptomethyl)benzene, 1,2,3,4-tetra(mercaptoethyl) base) benzene, 1,2,3,5-tetrakis(mercaptoethyl) ) benzene, 1,2,4,5-tetrakis(mercaptoethyl)benzene, 1,2,3,4-tetrakis(mercaptoethyl)benzene, 1,2,3,5-tetrakis(mercaptomethoxy) Benzene, 1,2,4,5-tetrakis(mercaptomethoxy)benzene, 1,2,3,4-tetrakis(mercaptoethoxy)benzene, 1,2,3,5-tetrakis(mercaptoethoxy) ) benzene, 1,2,4,5-tetra(mercaptoethoxy)benzene, 2,2′-dimercaptobiphenyl, 4,4′-dimercaptobiphenyl, 4,4′-dimercaptobibenzyl, 2,5-Toluene Dithiol, 3,4-Toluene Dithiol, 1,4-Naphthalene Dithiol, 1,5-Naphthalene Dithiol, 2,6-Naphthalene Dithiol, 2,7-Naphthalene Dithiol Dithiol, 2,4-dimethylbenzene-1,3-dithiol, 4,5-dimethylbenzene-1,3-dithiol, 9,10-anthracene dimethanethiol, 1, 3-bis(p-methoxyphenyl)propane-2,2-dithiol, 1,3-diphenylpropane-2,2-dithiol, phenylmethane-1,1-dithiol, Aromatic mercaptans such as 2,4-bis(p-mercaptophenyl)pentane; 2,5-dichlorobenzene-1,3-dithiol, 1,3-bis(p-chlorophenyl)propane-2, 2-dithiol, 3,4,5-tribromo-1,2-dimercaptobenzene, 2,3,4,6-tetrachloro-1,5-bis(mercaptomethyl)benzene and other salt substituents , bromine substituents and other halogen-substituted aromatic thiols; 1,2-bis(mercaptomethylthio)benzene, 1,3-bis(mercaptomethylthio)benzene, 1,4-bis(mercaptomethylthio) Benzene, 1,2-bis(mercaptoethylthio)benzene, 1,3-bis(mercaptoethylthio)benzene, 1,4-bis(mercaptoethylthio)benzene, 1,2,3-tri(mercapto Methylthio)benzene, 1,2,4-tris(mercaptomethylthio)benzene, 1,3,5-tris(mercaptomethylthio)benzene, 1,2,3-tris(mercaptoethylthio)benzene , 1,2,4-tri(mercaptoethylthio)benzene, 1,3,5-tri(mercaptoethylthio)benzene, 1,2,3,4-tetrakis(mercaptomethylthio)benzene, 1, 2,3,5-tetrakis(mercaptomethylthio)benzene, 1,2,4,5-tetrakis(mercaptomethylthio)benzene, 1,2,3,4-tetrakis(mercaptoethylthio)benzene, 1 , 2,3,5-Tetrakis(mercaptoethylthio)benzene, 1,2,4,5-tetrakis(mercaptoethylthio)benzene, etc., and their alkylated products containing sulfur atoms in addition to mercapto groups Mercaptans; bis(mercaptomethyl)sulfide, bis(mercaptoethyl)sulfide, bis(mercaptopropyl)sulfide, bis(mercaptomethylthio)methane, bis(2-mercaptoethylthio)methane , Bis(3-mercaptopropylthio)methane, 1,2-bis(mercaptomethylthio)ethane, 1,2-bis(2-mercaptoethylthio)ethane, 1,2-bis(3- Mercaptopropylthio)ethane, 1,3-bis(mercaptomethylthio)propane, 1,3-bis(2-mercaptoethylthio)propane, 1,3-bis(3-mercaptopropylthio)propane , 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, 2-mercaptoethylthio-1,3-propanedithiol, 1,2,3-tris(mercaptomethylthio)propane , 1,2,3-tris(2-mercaptoethylthio)propane, 1,2,3 - Tris(3-mercaptopropylthio)propane, tetrakis(mercaptomethylthiomethyl)methane, tetrakis(2-mercaptoethylthiomethyl)methane, tetrakis(3-mercaptopropylthiomethyl)methane, bis (2,3-dimercaptopropyl) sulfide, 2,5-dimercapto-1,4-dithiane, bis(mercaptomethyl) disulfide, bis(mercaptoethyl) disulfide, bis( Mercaptopropyl) disulfide, etc., and their thioglycolate and mercaptopropionate, hydroxymethyl sulfide bis(2-mercaptoacetate), hydroxymethyl sulfide bis(3-mercaptopropionate) ), hydroxyethyl sulfide bis(2-mercaptoacetate), hydroxyethyl sulfide bis(3-mercaptopropionate), hydroxypropyl sulfide bis(2-mercaptoacetate), hydroxypropyl Thioether bis(3-mercaptopropionate), hydroxymethyl disulfide bis(2-mercaptoacetate), hydroxymethyl disulfide bis(3-mercaptopropionate), hydroxyethyl disulfide Bis(2-mercaptoacetate), hydroxyethyl disulfide bis(3-mercaptopropionate), hydroxypropyl disulfide bis(2-mercaptoacetate), hydroxypropyl disulfide bis( 3-mercaptopropionate), 2-mercaptoethyl ether bis(2-mercaptoacetate), 2-mercaptoethyl ether bis(3-mercaptopropionate), 1,4-dithiane-2, 5-diol bis(2-mercaptoacetate), 1,4-dithiane-2,5-diol bis(3-mercaptopropionate), mercaptoacetic acid (2-mercaptoethyl ester), thio Bis(2-mercaptoethyl) dipropionate, bis(2-mercaptoethyl) 4,4'-thiodibutyrate, bis(2-mercaptoethyl) dithiodiacetate, dithiobis Bis(2-mercaptoethyl) propionate, bis(2-mercaptoethyl) 4,4′-dithiodibutyrate, bis(2,3-dimercaptopropyl) thiodiacetate, thio Bis(2,3-dimercaptopropyl) dipropionate, bis(2,3-dimercaptopropyl) dithiodiacetate, bis(2,3-dimercaptopropyl) dithiodipropionate , 4-mercaptomethyl-3,6-dithioctane-1,8-dithiol, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithia Undecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3 , 6,9-trithiaundecane, bis(1,3-dimercapto-2-propyl) sulfide and other aliphatic thiols containing sulfur atoms in addition to mercapto groups; 3,4-thiophenedithiol , 2,5-dimercaptomethyl-tetrahydrothiophene, 2,5-dimercapto-1,3,4-thiadiazole, 2,5-dimercapto-1,4-dithiane, 2,5- A heterocyclic compound containing a sulfur atom in addition to a mercapto group, such as dimercaptomethyl-1,4-dithiane.

<(A1-3) Polyol compound>

Examples of the polyol compound (hereinafter sometimes referred to simply as component (A1-3)) include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, neopentyl glycol, glycerin, trihydroxy Methylethane, trimethylolpropane, butanetriol, 1,2-methylglucoside, pentaerythritol, dipentaerythritol, tripentaerythritol, triethylene glycol, polyethylene glycol, tris(2-hydroxyethyl)iso Cyanurate, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, bicyclo[4.3.0]-nonanediol, dicyclohexanediol, tricyclo[ 5.3.1.1] Dodecanediol, spiro[3.4]octanediol, butylcyclohexanediol and other aliphatic polyols; dihydroxynaphthalene, trihydroxynaphthalene, tetrahydroxynaphthalene, dihydroxybenzene, benzenetriol, trihydroxynaphthalene Hydroxyphenanthrene, bisphenol A, bisphenol F, benzenedimethanol, tetrabromobisphenol A and other aromatic polyols, and their addition reaction products with alkylene oxides such as ethylene oxide or propylene oxide; bis-[ 4-(Hydroxyethoxy)phenyl]sulfide, bis-[4-(2-hydroxypropoxy)phenyl]sulfide, bis-[4-(2,3-dihydroxypropoxy)benzene base]sulfide, bis-[4-(4-hydroxycyclohexyloxy)phenyl]sulfide, bis-[2-methyl-4-(hydroxyethoxy)-6-butylphenyl]thio Ethers, and compounds in which an average of 3 molecules or less of ethylene oxide and/or propylene oxide are added to each hydroxyl group on these compounds; bis(2-hydroxyethyl)sulfide, 1,2-bis-(2 -Hydroxyethylmercapto)ethane, bis(2-hydroxyethyl)disulfide, 1,4-dithiane-2,5-diol, bis(2,3-dihydroxypropyl)sulfide, Tetrakis(4-hydroxy-2-thietyl)methane, bis(4-hydroxyphenyl)sulfone (trade name: bisphenol S), tetrabromobisphenol S, tetramethylbisphenol S, 4,4' - Sulfur-atom-containing polyhydric alcohols such as thiobis(6-tert-butyl-3-methylphenol), 1,3-bis(2-hydroxyethylthioethyl)-cyclohexane, and the like.

<(A1-4) Polyamine compound>

As said polyamine compound (it may abbreviate (A1-4) component hereinafter), for example, hexamethylenediamine and bis(4-aminocyclohexyl)methane are mentioned.

<(A2) Cationic polymerizable monomer>

Known monomers can be used as the cationically polymerizable monomer of the present invention without particular limitation, and are, for example, monomers used as raw materials for obtaining resins such as epoxy resins and polysulfide resins. Specifically, polyepoxides, polycyclic sulfur compounds, polythietane compounds, and monomers obtained by reacting polycyclic sulfur compounds and polythiol compounds as monomers for ring-opening polymerization, As the monomer, known polyepoxides (hereinafter sometimes referred to as (A2-1) component), polycyclic sulfur compounds (hereinafter sometimes referred to as (A2-2) component) or polysulfide compounds can be used without particular limitation. A heterocyclobutane compound (it may be abbreviated as (A2-3) component hereinafter). In addition, examples of the polythiol compound include those exemplified in the above (A1-2).

Hereinafter, the cationically polymerizable monomer will be described in detail.

<(A2-1) Polyepoxide>

As said polyepoxide compound, it can be roughly classified into an aliphatic epoxy compound, an alicyclic epoxy compound, and an aromatic epoxy compound, and the following compounds are mentioned as a specific example.

Examples of aliphatic epoxy compounds include: ethylene oxide, 2-ethyloxirane, butyl glycidyl ether, phenyl glycidyl ether, 2,2'-methylene diepoxy Ethane, 1,6-hexanediol diglycidyl ether, ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether ether, nonaethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, dipropylene glycol diglycidyl ether, tripropylene glycol diglycidyl ether, tetrapropylene glycol diglycidyl ether, nonapropylene glycol diglycidyl ether, Neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, glycerol triglycidyl ether, diglycerol tetraglycidyl ether, pentaerythritol tetraglycidyl ether, tris(2-hydroxyethyl ether) ) diglycidyl ether of isocyanurate, triglycidyl ether of tris(2-hydroxyethyl)isocyanurate.

Examples of the alicyclic epoxy compound include isophoronediol diglycidyl ether and bis-2,2-hydroxycyclohexylpropane diglycidyl ether.

Examples of the aromatic epoxy compound include: resorcinol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol S diglycidyl ether, ortho-phenol Diglycidyl Diformate, Novolac Polyglycidyl Ether, Cresol Novolac Polyglycidyl Ether.

<(A2-2) Polycyclic sulfur compounds>

Specific examples of the aforementioned polycyclic sulfur compounds include: bis(1,2-epithioethyl)sulfide, bis(1,2-epithioethyl)disulfide, bis(epithioethyl) ) methane, bis(thioethylthio)benzene, bis[4-(thioethylthio)phenyl]sulfide, bis[4-(thioethylthio)phenyl]methane, etc. base compounds; bis(2,3-epithiopropyl) sulfide, bis(2,3-epithiopropyl) disulfide, bis(2,3-epithiopropyl)methane, 1,2- Bis(2,3-epithiopropylthio)ethane, 1,2-bis(2,3-epithiopropylthio)propane, 1,3-bis(2,3-epithiopropylthio)propane , 1,3-bis(2,3-epithiopropylthio)-2-methylpropane, 1,4-bis(2,3-epithiopropylthio)butane, 1,4-bis(2 ,3-Epithiopropylthio)-2-methylbutane, 1,3-bis(2,3-epithiopropylthio)butane, 1,5-bis(2,3-epithiopropylthio) base) pentane, 1,5-bis(2,3-epithiopropylthio)-2-methylpentane, 1,5-bis(2,3-epithiopropylthio)-3-thia Pentane, 1,6-bis(2,3-epithiopropylthio)hexane, 1,6-bis(2,3-epithiopropylthio)-2-methylhexane, 1,8- Bis(2,3-epithiopropylthio)-3,6-dithiaoctane, 1,2,3-tris(2,3-epithiopropylthio)propane, 2,2-bis(2 ,3-Epithiopropylthio)-1,3-bis(2,3-epithiopropylthiomethyl)propane, 2,2-bis(2,3-epithiopropylthiomethyl)-1 -(2,3-Epithiopropylthio)butane, 1,5-bis(2,3-Epithiopropylthio)-2-(2,3-Epithiopropylthiomethyl)-3- Thiolane, 1,5-bis(2,3-epithiopropylthio)-2,4-bis(2,3-epithiopropylthiomethyl)-3-thiapentane, 1- (2,3-Epithiopropylthio)-2,2-bis(2,3-epithiopropylthiomethyl)-4-thiahexane, 1,5,6-tri(2,3- Epithiopropylthio)-4-(2,3-Epithiopropylthiomethyl)-3-thiahexane, 1,8-bis(2,3-Epithiopropylthio)-4-( 2,3-epithiopropylthiomethyl)-3,6-dithiaoctane, 1,8-bis(2,3-epithiopropylthio)-4,5-bis(2,3- Epithiopropylthiomethyl)-3,6-dithiaoctane, 1,8-bis(2,3-epithiopropylthio)-4,4-bis(2,3-epithiopropylthio) methyl)-3,6-dithiaoctane, 1,8-bis(2,3-epithiopropylthio)-2,5-bis(2,3-epithiopropylthiomethyl) -3,6-Dithiaoctane, 1,8-bis(2,3-epithiopropylthio)-2,4,5-tris(2,3-epithiopropylthiomethyl)-3 ,6-Dithiaoctane, 1,1,1-tris[[2-(2,3-epithiopropylthio)ethyl]thiomethyl]-2-(2,3-epithiopropylthio) Thio)ethane, 1,1,2,2-tetrakis[[2-(2,3-epithiopropylthio)ethyl]thio Methyl]ethane, 1,11-bis(2,3-epithiopropylthio)-4,8-bis(2,3-epithiopropylthiomethyl)-3,6,9-trisulfide Heteroundecane, 1,11-bis(2,3-epithiopropylthio)-4,7-bis(2,3-epithiopropylthiomethyl)-3,6,9-trithia Undecane, 1,11-bis(2,3-epithiopropylthio)-5,7-bis(2,3-epithiopropylthiomethyl)-3,6,9-trithiadeca Chain aliphatic 2,3-epithiopropylthio compounds such as alkane; 1,3-bis(2,3-epithiopropylthio)cyclohexane, 1,4-bis(2,3-cyclohexane Thiopropylthio)cyclohexane, 1,3-bis(2,3-epithiopropylthiomethyl)cyclohexane, 1,4-bis(2,3-epithiopropylthiomethyl)cyclohexane Hexane, 2,5-bis(2,3-epithiopropylthiomethyl)-1,4-dithiane, 2,5-bis[[2-(2,3-epithiopropylthio) Ethyl]thiomethyl]-1,4-dithiane, 2,5-bis(2,3-epithiopropylthiomethyl)-2,5-dimethyl-1,4-dithiane Cycloaliphatic 2,3-epithiopropylthio compounds such as alkanes; 1,2-bis(2,3-epithiopropylthio)benzene, 1,3-bis(2,3-epithiopropylthio) base) benzene, 1,4-bis(2,3-epithiopropylthio)benzene, 1,2-bis(2,3-epithiopropylthiomethyl)benzene, 1,3-bis(2, 3-epithiopropylthiomethyl)benzene, 1,4-bis(2,3-epithiopropylthiomethyl)benzene, bis[4-(2,3-epithiopropylthio)phenyl] Methane, 2,2-bis[4-(2,3-epithiopropylthio)phenyl]propane, bis[4-(2,3-epithiopropylthio)phenyl]sulfide, bis[4 Aromatic 2,3-epithiopropylthio compounds such as -(2,3-epithiopropylthio)phenyl]sulfone, 4,4'-bis(2,3-epithiopropylthio)biphenyl ; Bis(2,3-epithiopropyl) ether, bis(2,3-epithiopropoxy)methane, 1,2-bis(2,3-epithiopropoxy)ethane, 1,2 -Bis(2,3-epithiopropoxy)propane, 1,3-bis(2,3-epithiopropoxy)propane, 1,3-bis(2,3-epithiopropoxy)- 2-Methylpropane, 1,4-bis(2,3-epithiopropoxy)butane, 1,4-bis(2,3-epithiopropoxy)-2-methylbutane, 1 ,3-bis(2,3-epithiopropoxy)butane, 1,5-bis(2,3-epithiopropoxy)pentane, 1,5-bis(2,3-epithiopropoxy) Oxy)-2-methylpentane, 1,5-bis(2,3-epithiopropoxy)-3-thiopentane, 1,6-bis(2,3-epithiopropoxy ) hexane, 1,6-bis(2,3-epithiopropoxy)-2-methylhexane, 1,8-bis(2,3-epithiopropoxy)-3,6-bis Thia octane, 1,2,3-tris(2,3-epithiopropoxy)propane, 2,2-bis(2,3-epithiopropoxy)-1,3-bis(2, 3-epithiopropoxymethyl)propane, 2,2-bis(2,3-epithiopropoxymethyl)-1- (2,3-Epithiopropoxy)butane, 1,5-bis(2,3-Epithiopropoxy)-2-(2,3-Epithiopropoxymethyl)-3-thio Heteropentane, 1,5-bis(2,3-epithiopropoxy)-2,4-bis(2,3-epithiopropoxymethyl)-3-thiopentane, 1-( 2,3-epithiopropoxy)-2,2-bis(2,3-epithiopropoxymethyl)-4-thiahexane, 1,5,6-tri(2,3-cyclo Thiopropoxy)-4-(2,3-epithiopropoxymethyl)-3-thiahexane, 1,8-bis(2,3-epithiopropoxy)-4-(2 ,3-epithiopropoxymethyl)-3,6-dithia-octane, 1,8-bis(2,3-epithiopropoxy)-4,5-bis(2,3-cyclo Thiopropoxymethyl)-3,6-dithiaoctane, 1,8-bis(2,3-epithiopropoxy)-4,4-bis(2,3-epithiopropoxy) Methyl)-3,6-dithioctane, 1,8-bis(2,3-epithiopropoxy)-2,5-bis(2,3-epithiopropoxymethyl)- 3,6-Dithiaoctane, 1,8-bis(2,3-epithiopropoxy)-2,4,5-tris(2,3-epithiopropoxymethyl)-3, 6-Dithiaoctane, 1,1,1-tris[[2-(2,3-epithiopropoxy)ethyl]thiomethyl]-2-(2,3-epithiopropoxy base) ethane, 1,1,2,2-tetrakis[[2-(2,3-epithiopropoxy)ethyl]thiomethyl]ethane, 1,11-bis(2,3- Epithiapropoxy)-4,8-bis(2,3-epithiopropoxymethyl)-3,6,9-trithiaundecane, 1,11-bis(2,3-cyclo Thiopropoxy)-4,7-bis(2,3-epithiopropoxymethyl)-3,6,9-trithiaundecane, 1,11-bis(2,3-epithio Propoxy)-5,7-bis(2,3-epithiopropoxymethyl)-3,6,9-trithiaundecane and other chain aliphatic 2,3-epithiopropoxy 1,3-bis(2,3-epithiopropoxy)cyclohexane, 1,4-bis(2,3-epithiopropoxy)cyclohexane, 1,3-bis(2 ,3-Epithiopropoxymethyl)cyclohexane, 1,4-bis(2,3-epithiopropoxymethyl)cyclohexane, 2,5-bis(2,3-epithiopropane Oxymethyl)-1,4-dithiane, 2,5-bis[[2-(2,3-epithiopropoxy)ethyl]thiomethyl]-1,4-dithiane , 2,5-bis(2,3-epithiopropoxymethyl)-2,5-dimethyl-1,4-dithiane and other cycloaliphatic 2,3-epithiopropoxy groups Compound; 1,2-bis(2,3-epithiopropoxy)benzene, 1,3-bis(2,3-epithiopropoxy)benzene, 1,4-bis(2,3-epithiopropoxy) Propoxy)benzene, 1,2-bis(2,3-epithiopropoxymethyl)benzene, 1,3-bis(2,3-epithiopropoxymethyl)benzene, 1,4- Bis(2,3-epithiopropoxymethyl)benzene, bis[4-(2,3-epithiopropoxy)phenyl]methane, 2,2-bis[ 4-(2,3-Epithiopropoxy)phenyl]propane, Bis[4-(2,3-Epithiopropoxy)phenyl]sulfide, Bis[4-(2,3-Epithiopropoxy) Propoxy)phenyl]sulfone, 4,4'-bis(2,3-epithiopropoxy)biphenyl and other aromatic 2,3-epithiopropoxy compounds, etc.

<(A2-3) Polythietane compound>

As the polythietane compound, a metal-containing thietane compound or a non-metal thietane compound can be used. These polythietane compounds contain one or more thietanyl groups in the molecule as disclosed in WO2005/095490 and JP-A-2003-327583. It is preferably a compound containing two or more thietanyl groups in total. Examples include: dithietanylsulfide, bis(3-thietanylthio)disulfide, bis(3-thietanylthio)methane, 3-( ((3′-Thietylthio)methylthio)methylthio)thietane and other sulfide-based thietane compounds; bis(3-thietanyl)di Sulfide, bis(3-thietanyl) trisulfide, bis(3-thietanyl) tetrasulfide, bis(3-thietanyl) pentasulfide and other polysulfides It is a thietane compound, etc.

<(A3) Radical polymerizable monomer>

Known monomers can be used as the radically polymerizable monomer of the present invention without particular limitation, for example, a (meth)acrylate compound (hereinafter sometimes simply referred to as component (A3-1)) can be used alone or in combination, A radically polymerizable monomer having a meth)acrylate group but having a carbon-carbon unsaturated bond (hereinafter may be simply referred to as an ethylenic compound or a component (A3-2)).

<(A3-1) (meth)acrylate compound>

As the (meth)acrylate compound, known compounds having at least one (meth)acrylate group in the molecule can be used without particular limitation, and examples of specific (meth)acrylate compounds include glycidol base (meth)acrylate, trimethylolpropane tri(meth)acrylate, tetramethylolmethane tri(meth)acrylate, trimethylolpropane triethylene glycol tri(meth)acrylate, Pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, urethane oligomer tetra(meth)acrylate, urethane oligomer hexa(meth)acrylate, poly Ester oligomer hexa(meth)acrylate, ethylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, polyethylene glycol di(meth)acrylate (Meth)acrylate (especially average molecular weight 308, 330, 508, 736), tripropylene glycol di(meth)acrylate, bisphenol A-di(meth)acrylate, 2,2-bis[4 -((meth)acryloyloxypolyethoxy)phenyl]propane (especially average molecular weight 478, 776, 804), methoxypolyethylene glycol (meth)acrylate, methoxypolyethylene glycol Ethylene glycol (meth)acrylate (particularly, the average molecular weight is 468), methyl (meth)acrylate, etc.

<(A3-2) Olefinic compound>

Examples of specific olefinic compounds include: methyl vinyl ketone, ethyl vinyl ketone, ethyl vinyl ether, styrene, vinyl cyclohexane, butadiene, and 1,4-pentadiene , divinyl sulfide, divinyl sulfone, 1,2-divinylbenzene, 1,3-divinyl-1,1,3,3-tetramethylpropane disiloxane, diethylene glycol di Vinyl ether, divinyl adipate, divinyl sebacate, ethylene glycol divinyl ether, divinyl sulfoxide, divinyl persulfide, dimethyldivinylsilane, 1,2 , 4-trivinylcyclohexane, methyltrivinylsilane, α-methylstyrene and α-methylstyrene dimer, etc.

In addition, diethylene glycol bisallyl carbonate, methoxypolyethylene glycol allyl ether (especially with an average molecular weight of 550), methoxypolyethylene glycol allyl ether (especially The average molecular weight is 350), methoxypolyethylene glycol allyl ether (especially the average molecular weight is 1500), polyethylene glycol allyl ether (especially the average molecular weight is 450), methoxypolyethylene glycol -Polypropylene glycol allyl ether (especially with an average molecular weight of 750), butoxypolyethylene glycol-polypropylene glycol allyl ether (especially with an average molecular weight of 1600), methacryloxypolyethylene glycol- Polypropylene glycol allyl ether (especially the average molecular weight of 560), phenoxy polyethylene glycol allyl ether (especially the average molecular weight of 600), methacryloxy polyethylene glycol allyl ether ( Especially with an average molecular weight of 430), acryloxypolyethylene glycol allyl ether (especially with an average molecular weight of 420), ethyleneoxypolyethylene glycol allyl ether (especially with an average molecular weight of 560), benzene Ethyleneoxypolyethylene glycol allyl ether (especially with an average molecular weight of 650), methoxypolyethylenethioglycol allylthio ether (especially with an average molecular weight of 730), etc.

As the polymerizable monomer (A), the following combinations are preferable: a combination of a polyisocyanate compound and a polythiol compound, a combination of a polyisocyanate compound and a polyol compound, a polycyclic sulfur compound and/or a polythietane compound , A combination of a polycyclic sulfur compound and a polythiol compound.

Moreover, among the above, the polymerizable monomer (A) is more preferably a combination of a polyisocyanate compound and a polythiol compound, or a combination of a polycyclic sulfur compound and a polythiol compound.

When the polymerizable monomer (A) is a combination of a polyisocyanate compound and a polythiol compound, in particular, the polymerizable monomer (A) preferably contains: , xylylene diisocyanate, diphenylmethane diisocyanate, and at least one polyisocyanate compound in toluene diisocyanate, and, selected from pentaerythritol tetrakis (3-mercaptopropionate) ester and 1,2-bis (2 - At least one polythiol compound in -mercaptoethylthio)-3-mercaptopropane.

When the polymerizable monomer (A) is a combination of an episulfide compound and a polythiol compound, the polymerizable monomer (A) particularly preferably contains: bis(2,3-epithiopropyl) disulfide, and 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9 - A mixture of trithiaundecane and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components.

<(B) Benzotriazole-based ultraviolet absorbers with a maximum absorption wavelength of 360 nm or more and less than 380 nm>

In the present invention, (B) a benzotriazole-based ultraviolet absorber (hereinafter sometimes referred to simply as component (B)) having a maximum absorption wavelength of 360 nm or more and less than 380 nm is contained in order to impart the ability to block ultraviolet rays and blue light to the optical material. .

The benzotriazole-based ultraviolet absorbent of the present invention is represented by the following formula (1).

In the present invention, the maximum absorption wavelength refers to the wavelength of the vertex of the maximum absorption (the vertex of the convex spectrum) appearing in the absorption spectrum. In addition, a plurality of maximum absorption wavelengths may be observed. In such a case, it is only necessary to confirm that at least one maximum absorption wavelength is within the wavelength range specified in the present invention. For example, the above-mentioned benzotriazole-based ultraviolet absorber whose maximum absorption wavelength is 360 nm to less than 380 nm refers to a benzotriazole-based ultraviolet absorber in which at least one of the maximum absorption wavelengths is 360 nm to less than 380 nm. .

[Chem 2]

(Wherein, R1 represents a hydrogen atom, an alkyl group with ¹ to 8 carbons, an alkoxy group with 1 to 8 carbons, a hydroxyl group, a linear or branched monosubstituted amino group with 1 to 4 carbons, a single substituted amino group with 1 to 8 carbons, 4 linear or branched disubstituted amino groups, nitro groups, carboxyl groups, alkoxycarbonyl groups with 1 to 8 carbon atoms, hydroxyalkyl groups with 1 to 8 carbon atoms, and alkyl groups with 1 to 8 carbon atoms each Alkylcarbonyloxyalkyl of 8, carboxyalkyl with 1 to 3 carbon atoms in the alkyl group, alkoxycarbonylalkyl group with 2 to 10 carbon atoms in total in the alkyl group, aryl group, acyl group, sulfo group or cyano group R ² represents hydroxyl, alkoxy with 1 to 8 carbons, alkylthio with 1 to 8 carbons, linear or branched monosubstituted amino with 1 to 4 carbons, straight or branched amino with 1 to 4 carbons Chain or branched disubstituted amino; R ³ represents a hydrogen atom, hydroxyl, alkyl or alkoxy with 1 to 8 carbons, straight or branched monosubstituted amino with 1 to 4 carbons, 1 to 8 carbons 4 straight-chain or branched disubstituted amino, also can be R ² and R ³ cross-linked ring structure.)

In the general formula ( ¹ ), specific examples of R include: a hydrogen atom; methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl , n-hexyl, n-octyl, 2-ethylhexyl and other linear or branched alkyl groups with 1 to 8 carbons that can be substituted; methoxy, ethoxy, propoxy, isopropoxy, n- Butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-hexyloxy, n-octyloxy, 2-ethylhexyloxy, etc. can be substituted straight or branched chains with 1 to 8 carbons Alkoxy; hydroxyl; amino, monomethylamino, dimethylamino, monoethylamino, diethylamino, mono-n-propylamino, di-n-propylamino, monoisopropylamino, diisopropylamino, etc. 1 to 4 linear or branched amino groups; nitro; carboxyl; methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-hexyloxycarbonyl, n-octyloxycarbonyl, 2-ethylhexyloxycarbonyl and other substitutable straight-chain or branched alkoxycarbonyl groups with 1-8 carbon atoms; hydroxymethyl, hydroxyethyl, hydroxypropyl Substitutable linear or branched hydroxyalkyl groups with 1 to 8 carbons such as hydroxybutyl, hydroxyhexyl, hydroxyoctyl; methylcarbonyloxymethyl, ethylcarbonyloxymethyl, propyl Carbonyloxymethyl, Butylcarbonyloxymethyl, Hexylcarbonyloxymethyl, Heptylcarbonyloxymethyl, Octylcarbonyloxymethyl, Methylcarbonyloxyethyl, Ethylcarbonyloxy The carbon number of the alkyl group that can be substituted, such as ethyl, propylcarbonyloxyethyl, butylcarbonyloxyethyl, hexylcarbonyloxyethyl, heptylcarbonyloxyethyl, octylcarbonyloxyethyl, etc. Linear or branched alkylcarbonyloxyalkyl groups each of 1 to 8; carboxymethyl, carboxyethyl, carboxypropyl and other carboxyalkyl groups; methoxycarbonylmethyl, ethoxycarbonylethyl, propyl Straight-chain or branched alkoxycarbonylalkyl groups such as oxycarbonylethyl and other alkyl groups each having 1 to 8 carbon atoms; aryl groups such as phenyl, benzyl, tolyl, xylyl, etc.; formyl, acetyl, Acyl groups such as propionyl, butyryl, and benzoyl; sulfo; cyano, etc. ^In addition, specific examples of R2 include: hydroxyl; methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy Straight-chain or branched alkoxy groups with 1 to 8 carbons that can be substituted, such as n-hexyloxy, n-octyloxy, 2-ethylhexyloxy; methylthio, ethylthio, propylthio, Isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio, n-hexylthio, n-octylthio, 2-ethylhexylthio and other substitutable carbon numbers 1 to 8 straight-chain or branched alkylthio; monomethylamino, dimethylamino, monoethylamino, diethylamino, mono-n-propylamino, di-n-propylamino, monoisopropylamino, diisopropylamino, etc. can be substituted A linear or branched amino group having 1 to 4 carbon atoms, etc. Specific examples of ^R3 include: hydrogen atom; hydroxyl group; methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-hexyl, n-octyl Straight-chain or branched-chain alkyl groups with 1 to 8 carbon atoms that can be substituted, such as 2-ethylhexyl; methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutyl Oxygen, sec-butoxy, tert-butoxy, n-hexyloxy, n-octyloxy, 2-ethylhexyloxy and other linear or branched alkoxy groups with 1 to 8 carbons; Straight-chain or branched chains with 1 to 4 carbons that can be substituted, such as methylamino, dimethylamino, monoethylamino, diethylamino, mono-n-propylamino, di-n-propylamino, monoisopropylamino, diisopropylamino, etc. Amino, etc. In addition, in the case of a ring structure in which R ² and R ³ are cross-linked, methylenedioxy, ethylenedioxy, etc. are mentioned.

Among the benzotriazole derivative compounds represented by the above general formula (1), it is particularly preferable that R ¹ is a hydrogen atom, a methyl group, a methoxy group, n-octyloxy group, a hydroxyl group, a carboxyl group, or a methoxycarbonyl group. , ethoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-hexyloxycarbonyl, n-octyloxycarbonyl, hydroxyethyl, methylcarbonyloxyethyl , heptylcarbonyloxyethyl, as R ² , is methoxy, ethoxy, n-octyloxy, dimethylamino, diethylamino, as R ³ , is a hydrogen atom, methyl, ethyl, methyl Oxygen, ethoxy, n-octyloxy, dimethylamino, when R ² and R ³ are cross-linked ring structures, are methylenedioxy.

Here, from the viewpoint of the maximum absorption wavelength, it is preferable that R ² or R ² and R ³ select an electron-donating substituent, and/or R ¹ select an electron-withdrawing substituent.

Examples of electron-donating substituents include: hydroxyl group, alkoxy group having 1 to 8 carbons, alkylthio group having 1 to 8 carbons, linear or branched monosubstituted amino group having 1 to 4 carbons, carbon 1-4 linear or branched disubstituted amino groups. As described above, ^R2 and ^R3 are electron ^- donating substituents when R2 and ^R3 are crosslinked and form a methylenedioxy group. Moreover, examples of the electron-withdrawing substituent include a nitro group, a carboxyl group, an alkoxycarbonyl group, an acyl group, a sulfo group, and a cyano group.

英-6-醇、7-(5-丁氧羰基-2H-苯并三唑-2-基)苯并[1,4]二

英-6-醇、7-(5-辛氧羰基-2H-苯并三唑-2-基)苯并[1,4]二

英-6-醇、7-(5-甲基-2H-苯并三唑-2-基)苯并[1,4]二

英-6-醇等。Examples of the benzotriazole derivative compound represented by the general formula (1) of the present invention include: 2-(2-hydroxy-4-dimethylaminophenyl)-5-methoxycarbonyl-2H-benzo Triazole, 2-(2-hydroxy-4-dimethylaminophenyl)-5-ethoxycarbonyl-2H-benzotriazole, 2-(2-hydroxy-4-dimethylaminophenyl)-5- Butoxycarbonyl-2H-benzotriazole, 2-(2-hydroxy-4-dimethylaminophenyl)-5-octyloxycarbonyl-2H-benzotriazole, 2-(2-hydroxy-4-di Methylaminophenyl)-5-methyl-2H-benzotriazole, 2-(2-hydroxy-4-diethylaminophenyl)-5-butoxycarbonyl-2H-benzotriazole, 2-( 2-Hydroxy-4-dimethylamino-5-methylphenyl)-5-methoxycarbonyl-2H-benzotriazole, 2-(2-hydroxy-4-dimethylamino-5-methylphenyl )-5-butoxycarbonyl-2H-benzotriazole, 2-(2-hydroxy-4-dimethylamino-5-methylphenyl)-5-octyloxycarbonyl-2H-benzotriazole, 2 -(2-Hydroxy-4-dimethylamino-5-methylphenyl)-5-methyl-2H-benzotriazole, 2-(2-hydroxy-4,5-dimethoxyphenyl) -5-methoxycarbonyl-2H-benzotriazole, 2-(2-hydroxy-4,5-dimethoxyphenyl)-5-butoxycarbonyl-2H-benzotriazole, 2-(2 -Hydroxy-4,5-dimethoxyphenyl)-5-octyloxycarbonyl-2H-benzotriazole, 2-(2-hydroxy-4,5-dimethoxyphenyl)-5-methyl Base-2H-benzotriazole, 6-(5-heptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxole-5- Alcohol, 6-(5-isoheptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol, 6-(5 -Octyloxy-2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol, 6-(5-methylcarbonyloxyethyl-2H- Benzotriazol-2-yl)benzo[1,3]dioxol-5-ol, 7-(5-methoxycarbonyl-2H-benzotriazol-2-yl)benzo [1,4] two

Ying-6-ol, 7-(5-butoxycarbonyl-2H-benzotriazol-2-yl)benzo[1,4]di

Ying-6-ol, 7-(5-octyloxycarbonyl-2H-benzotriazol-2-yl)benzo[1,4]di

Ying-6-ol, 7-(5-methyl-2H-benzotriazol-2-yl)benzo[1,4]di

Ying-6-ol, etc.

In the above formula (1), the component (B) is preferably a compound in which R ² and R ³ are cross-linked to form a methylenedioxy group. Specifically, as component (B), 6-(5-heptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxole- 5-alcohol, 6-(5-isoheptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol, 6- (5-octyloxy-2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol, 6-(5-methylcarbonyloxyethyl- 2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol, etc., among which 6-(5-heptylcarbonyloxyethyl-2H- benzotriazol-2-yl)benzo[1,3]dioxol-5-ol.

It is preferable that the light absorption coefficient of the said (B) component is the range of 10-200 (L/(g·cm)) in order to make operability favorable and to exhibit an effect effectively. By satisfying this range, it is possible to obtain an effect of excellent blocking performance against ultraviolet rays and blue light without lowering the strength of an optical material obtained by polymerizing and curing the composition for an optical material.

In addition, by making the compounding amount of the above-mentioned (B) component 0.005 to 0.3 parts by mass with respect to 100 parts by mass of the above-mentioned (A) component, there is an effect that the ability to block ultraviolet rays and blue light is excellent, and it can be obtained without reducing the optical material. Polymerization curing is carried out under the condition of high strength. In order to further enhance this effect, it is more preferable that the compounding quantity of the said (B) compound is 0.01-0.2 mass part.

The ultraviolet absorber of the composition for optical materials of this invention containing the said (A) component and (B) component is hard to precipitate, and is excellent in long-term storage stability.

<additive>

For polymerization curing, a polymerization catalyst or a polymerization initiator may be added to the composition for an optical material of the present invention as needed. In addition, as long as the effect is not impaired, the composition for optical materials of the present invention may contain various known compounding ingredients such as antistatic agents, internal release agents, antioxidants, anticoloring agents, Fluorescent dyes, dyes, pigments, fragrances, solvents, leveling agents, resin modifiers, light stabilizers, infrared absorbers, visible light absorbers, etc. Furthermore, in addition to the above-mentioned ultraviolet absorber, a known ultraviolet absorber having a maximum absorption wavelength other than the range of 360 nm to less than 380 nm may be contained.

· Polymerization catalyst

盐类、路易斯酸类、或有机磺酸。As polymerization catalysts, tertiary amines and their corresponding inorganic or organic salts, phosphines, quaternary ammonium salts, quaternary

salts, Lewis acids, or organic sulfonic acids.

If the specific reaction catalyst is illustrated, the following are mentioned.

Tertiary amines; triethylamine, tripropylamine, dipropylethylamine, tributylamine, dimethylcyclohexylamine, triethylenediamine, tetramethylethylenediamine, N,N-dicyclohexylmethyl Amine, N,N-diisopropylethylamine, N-isopropyl-N-methylbutylamine, N-methylpiperidine, N-ethylpiperidine, N,N-dimethylpiperazine, N,N-diethylpiperazine, hexamethylenetetramine, N-methylmorpholine, N-ethylmorpholine, N-methylpiperidone, N-methylpyrrolidine, N-ethyl Pyrrolidine, N-Methylpyrrolidone, N,N-Dimethylbenzylamine, N,N-Dimethylaniline, N-Methyldibenzylamine, Pyridine, N-Methylpyrazole, 1-Methylimidazole , 1,2-dimethylimidazole, benzylmethylimidazole, N-methylpyrrole, diphenylmethylamine.

Phosphine: trimethylphosphine, triethylphosphine, tri-n-propylphosphine, triisopropylphosphine, tri-n-butylphosphine, triphenylphosphine, tribenzylphosphine, 1,2-bis(diphenyl Phosphine)ethane, 1,2-bis(dimethylphosphino)ethane.

Quaternary ammonium salts: tetramethyl ammonium bromide, tetrabutyl ammonium chloride, tetrabutyl ammonium bromide, triethyl benzyl ammonium chloride, hexadecyl dimethyl benzyl ammonium chloride, 1- n-dodecyl pyridinium chloride.

盐类：四甲基溴化

、四丁基氯化

、四丁基溴化

、四苯基溴化

。season

Salts: Tetramethyl bromide

, tetrabutyl chloride

, tetrabutyl bromide

, tetraphenyl bromide

.

Lewis acid: triphenyl aluminum, dimethyl tin dichloride, bis(isooctyl mercaptoacetate) dimethyl tin, dibutyl tin dichloride, dibutyl tin dilaurate, dibutyl tin maleate, maleate Dibutyltin toate polymer, dibutyltin diricinoleate, dibutyltin bis(dodecylmercaptan), dibutyltin bis(isooctyl mercaptoacetate), dioctyltin dichloride, dioctyltin maleate, Dioctyltin maleate polymer, dioctyltin bis(butylmaleate), dioctyltin dilaurate, dioctyltin diricinoleate, dioctyltin dioleate, dioctyltin di(6-hydroxy)hexanoate, bis Dioctyltin (isooctylthioglycolate), didodecyltin diricinoleate; various other metal salts, for example, copper oleate, copper acetylacetonate, iron acetylacetonate, iron naphthenate, Ferric lactate, ferric citrate, ferric gluconate, potassium caprylate, 2-ethylhexyl titanate.

Organic sulfonic acids: methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid.

The addition amount of a polymerization catalyst is suitably 0.001-1 mass part, Preferably it is 0.002-0.5 mass part, More preferably, it is 0.005-0.4 mass part with the total amount of (A) component being 100 mass parts.

· Polymerization Initiator

As the polymerization initiator, known thermal polymerization initiators, photopolymerization initiators, and the like can be used without particular limitation. When a typical polymerization initiator is illustrated, the following polymerization initiators are mentioned.

Thermal polymerization initiators: benzoyl peroxide, p-chlorobenzoyl peroxide, decanoyl peroxide, lauroyl peroxide, acetyl peroxide and other diacyl peroxides; tert-butyl peroxide 2-ethylhexanoate, Peroxyesters such as tert-butyl peroxyneodecanoate, cumyl peroxyneodecanoate, tert-butyl peroxybenzoate, etc.; peroxyesters such as diisopropyl peroxydicarbonate, di-sec-butyl peroxydicarbonate, etc. Oxygenated carbonates; azo compounds such as azobisisobutyronitrile, etc.

Photopolymerization initiators: benzophenone; 2,2-dimethoxy-1,2-diphenylethan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl -1-phenylpropan-1-one, 1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one, 2-methyl -1-[4-(methylthio)phenyl]-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butan Ketone-1,1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one and other acetophenone compounds; 1,2-diphenylethanedione, methyl α-dicarbonyl compounds such as phenylglyoxylate; 2,6-dimethylbenzoyldiphenylphosphine oxide, bis(2,4,6-trimethylbenzoyl)-phenylphosphine oxide , bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphosphine oxide, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2 ,4,6-Trimethylbenzoyldiphenylphosphonic acid methyl ester, 2,6-dichlorobenzoyldiphenylphosphine oxide, 2,6-dimethoxybenzoyldiphenylphosphine oxide Other acyl phosphine oxide compounds; 1,2-octanedione-1-[4-(phenylthio)-2-(O-benzoyl oxime)] and so on.

The amount of polymerization initiator added is preferably 0.01 to 0.5 parts by mass, more preferably 0.05 to 0.4 parts by mass, based on 100 parts by mass of the total amount of (A) components.

·Internal release agent

Examples of internal release agents include: fluorine-based nonionic surfactants, silicon-based nonionic surfactants, alkyl quaternary ammonium salts, phosphoric acid esters, acidic phosphoric esters, oxyalkylene-type acidic phosphoric esters, acidic Alkali metal salts of phosphate esters, alkali metal salts of oxyalkylene-type acid phosphate esters, metal salts of higher fatty acids, higher fatty acid esters, paraffins, waxes, higher aliphatic amides, higher aliphatic alcohols, polysiloxanes Classes, aliphatic amine oxirane adducts, etc. For example, as the acidic phosphate ester, ZelecUN manufactured by STEPAN Co., Ltd., internal release agent for MR manufactured by Mitsui Chemicals, JP series manufactured by Johoku Chemical Industry Co., Ltd., Phospharol series manufactured by Toho Chemical Industry Co., Ltd., AP, DP series, etc. manufactured by Daihachi Chemical Industry Co., Ltd.

·Resin modifier

In order to adjust various physical properties such as optical properties of the resin, impact resistance, and specific gravity, and to adjust the viscosity and pot life of the composition for optical materials, within the range that does not impair the effect of this embodiment, the combination for optical materials of the present invention can be Add resin modifier to the compound. For example, episulfide compounds, alcohol compounds, amine compounds, epoxy compounds, organic acids and their anhydrides, olefin compounds containing (meth)acrylate compounds, and the like can be used.

·Visible light absorber

As the visible light absorber, any compound can be used without particular limitation as long as the maximum absorption wavelength is in the range of 400 nm to 750 nm. For example, perylene-based compounds, porphyrin compounds, carotenoid-based compounds, cyanine-based compounds, phthalocyanine-based compounds, anthraquinone-based compounds, indigo-based compounds, neodymium compounds, porphyrazine compounds, and the like can be used.

<Optical material>

The optical material of the present invention includes a cured product obtained by polymerizing and curing the above composition for an optical material. The optical material preferably has a light transmittance of 5% or less at a wavelength of 400nm and a light transmittance of 70% or less at a wavelength of 420nm, and a light blocking rate (also referred to as a blue light blocking rate) of 35% in the wavelength region of 380 to 500nm. above.

The light transmittance of the optical material at a wavelength of 400 nm is more preferably 3% or less, and still more preferably 1% or less.

The light transmittance of the optical material at a wavelength of 420 nm is more preferably 65% or less, still more preferably 60% or less.

The light blocking rate in the wavelength region of 380 to 500 nm is more preferably 38% or more, and still more preferably 40% or more.

It should be noted that regarding the light blocking rate in the wavelength range of 380 to 500 nm, the transmittance is calculated every 10 nm in the wavelength range of 380 nm to 500 nm, and the average value of the transmittance at intervals of 10 nm (also referred to as the transmittance of 380 to 500 nm) The average value of the rate (T)) was calculated and obtained by the following formula.

Blue light blocking rate=100-(the average value of transmittance (T) from 380 to 500nm)

The application of the optical material obtained by polymerizing and curing the composition for optical material of the present invention is not particularly limited, and it can be applied to ordinary spectacle lenses, goggles, spectacle lenses for vision correction, lenses for imaging equipment, and Fresnel for liquid crystal projectors. Various plastic lenses such as ear lenses, biconvex lenses, and contact lenses.

As a method for producing an optical material, a method may be mentioned in which one or more benzotriazole-based ultraviolet absorbers selected from the above formula (1) are mixed with a polymerizable monomer to form a composition for an optical material, and then Polymerization curing and shaping are performed using known manufacturing methods.

The method for producing the above-mentioned plastic lens using the composition for optical materials is not particularly limited, and casting polymerization is generally used. For example, if necessary, a polymerization initiator is mixed with a composition for optical materials, the mixture is poured into a mold for lens molding, and usually heated at -20°C to 150°C to obtain a plastic lens.

<Secondary processing of optical materials: lamination of coatings>

An optical material obtained by polymerizing and curing the composition for an optical material of the present invention, particularly a plastic lens containing the above-mentioned optical material, can be used by coating one or both surfaces as necessary.

Specific examples of the coating layer include a primer layer, a hard coat layer, an antireflection layer, an antifogging layer, an antifouling layer, and a water-repellent layer. These coating layers may be used alone, or a plurality of coating layers may be used as a multilayer. When coatings are applied on both sides, either the same coating or different coatings may be applied to each side.

These coatings may be combined with a known ultraviolet absorber, an infrared absorber for protecting eyes from infrared rays, a light stabilizer or an antioxidant for improving the weather resistance of the lens, and a dye or pigment for improving the fashion of the lens. , and photochromic dyes or photochromic pigments, antistatic agents, and known additives for improving lens performance may be used in combination. Regarding the layer to which the paint is applied by coating, various leveling agents for improving coatability can be used.

When forming the hard coat layer, it is obtained by applying and curing a coating solution containing particulate inorganic substances such as organosilicon compounds, tin oxide, silicon oxide, zirconium oxide, and titanium oxide. In addition, a primer layer mainly composed of polyurethane may be provided on the surface of the plastic lens in order to improve the impact resistance or the adhesion with the hard coat layer. Furthermore, in order to impart antireflection performance, an antireflection layer may be applied on the hard coat layer using silicon oxide, titania, zirconia, tantalum oxide, or the like. Furthermore, in order to improve hydrophobicity, a hydrophobic film may be applied on the antireflection layer using an organosilicon compound having fluorine atoms.

Example

Hereinafter, although an Example is given and this invention is demonstrated concretely, this invention is not limited to these Examples.

The physical properties of the plastic lens obtained by polymerizing and curing the composition for an optical material were determined by the following method.

(1) Measurement of light transmittance at 400nm and 420nm

The transmittance at a wavelength of 380 to 800 nm was measured using a spectrophotometer (UV-2550, manufactured by Shimadzu Corporation), and the light transmittance and visual transmittance at the above wavelengths were determined.

(2) Measurement of the light blocking rate in the blue region (380nm to 500nm wavelength region)

The transmittance at a wavelength of 380 to 500 nm was measured using a spectrophotometer (UV-2550, manufactured by Shimadzu Corporation), and the blue light blocking rate was calculated by the following formula from the transmittance (T (%)) at every 10 nm.

Blue light blocking rate (%)=100-(the average value of transmittance (T) from 380 to 500nm)

The maximum absorption wavelength of the ultraviolet absorber is obtained by the following method.

As a measuring instrument, Shimadzu Spectrophotometer UV-2550 manufactured by Shimadzu Corporation was used. The measurement was performed by preparing a solution (concentration: 1.0×10 ^-4 mol/L) of the object to be measured dissolved in a solvent (chloroform), and measuring using a quartz cell with an optical path length of 10 mm.

Example 1

In 50.28 parts by mass of bis(isocyanatomethyl)bicyclo[2.2.1]heptane, 0.06 parts by mass of dimethyltin dichloride as a catalyst and acidic phosphate JP-506H as a release agent were added (Chengbei Chemical Industry Co., Ltd. Co., Ltd.) 0.15 parts by mass, 6-(5-heptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxol as an ultraviolet absorber En-5-ol (maximum absorption wavelength: 367nm) 0.04 parts by mass, after stirring and mixing, further add 25.50 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) ester, 1,2-bis(2-mercaptoethylthio) - 24.22 parts by mass of 3-mercaptopropane were stirred and mixed for 30 minutes under a reduced pressure of 10 mmHg to prepare a composition for optical materials. Next, this optical material composition was poured into a previously prepared lens-molding mold (2.0 mm in center thickness) including a glass mold and a resin pad, and placed in an electric furnace at 20° C. to 120° C. for 24 hours to perform polymerization. After the polymerization, the pad and the mold were taken out, and then heat-treated at 120° C. for 2 hours to obtain a plastic lens. Table 1 shows the evaluation results of the obtained lenses.

Example 2

To 52.02 parts by mass of xylylene diisocyanate, add 0.04 parts by mass of dimethyl tin dichloride as a catalyst, 0.15 parts by mass of acidic phosphate ester JP-506H (manufactured by Johoku Chemical Industry Co., Ltd.) as a release agent, as 6-(5-Heptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol (maximum absorption Wavelength: 367nm) 0.04 parts by mass, after stirring and mixing, further add 47.98 parts by mass of 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane, and stir and mix under a reduced pressure of 10mmHg for 30 minutes to prepare an optical material with composition. The composition for optical materials was poured into a pre-prepared lens molding mold (2.0 mm in center thickness) including a glass mold and a resin pad, and placed in an electric furnace at 20° C. to 120° C. for 24 hours to perform polymerization. After the polymerization, the pad and the mold were taken out, and then heat-treated at 120° C. for 2 hours to obtain a plastic lens. Table 1 shows the evaluation results of the obtained lenses.

Example 3

Charge a well-dried flask with 6-(5-heptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol (Maximum absorption wavelength: 367 nm) 0.04 parts by mass, 90.9 parts by mass of bis(2,3-epithiopropyl)disulfide, stirred at 20° C. for 1 hour, and prepared a solution. To this solution, 0.019 parts by mass of N,N-dimethylcyclohexylamine and 0.09 parts by mass of N,N-dicyclohexylmethylamine were dissolved in 5,7-dimercaptomethyl-1,11-dimercapto -3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane and 4,8-dimercaptomethyl A solution obtained in 9.1 parts by mass of a mixture containing 1,11-dimercapto-3,6,9-trithiaundecane as the main component was stirred at 20° C. for 30 minutes to prepare a composition for an optical material. The composition for optical materials was defoamed at 600 Pa for 1 hour, and after filtering through a 1 μm PTFE filter, the composition for optical materials was poured into a mold (center thickness 2.0 mm). The glass mold was left at 30°C to 80°C for 21 hours to perform polymerization. After the polymerization, the mat and the mold were taken out, and then heat-treated at 120° C. for 3 hours to obtain a plastic lens. Table 1 shows the evaluation results of the obtained lenses.

Example 4

90.00 parts by mass of methyl methacrylate, 10.00 parts by mass of ethylene glycol dimethacrylate, 6-(5-heptylcarbonyloxyethyl-2H-benzotriazol-2-yl as an ultraviolet absorber ) 0.04 parts by mass of benzo[1,3]dioxol-5-ol (maximum absorption wavelength: 367nm) and 0.10 parts by mass of azobisisobutyronitrile as a thermal polymerization initiator were mixed in After stirring well at room temperature, the pressure was reduced to 50 mmHg, and degassed for 10 minutes to obtain a composition for an optical material. Next, this optical material composition was poured into a previously prepared lens-molding mold (2.0 mm in center thickness) including a glass mold and a resin pad, and placed in an electric furnace at 40° C. to 85° C. for 24 hours to perform polymerization. After the polymerization, the mat and the mold were taken out, and then heat-treated at 100° C. for 2 hours to obtain a plastic lens. Table 1 shows the evaluation results of the obtained lenses.

Embodiment 5-8

In Examples 1-4, except having changed the addition amount of an ultraviolet absorber as shown in Table 1, it carried out similarly to Examples 1-4, and obtained the plastic lens. Table 1 shows the evaluation results of the obtained lenses.

It was confirmed that the compositions for optical materials prepared in Examples 1 to 8 above did not precipitate the ultraviolet absorber within 24 hours at room temperature (25° C.), and were excellent in long-term storage stability.

Comparative example 1, 2

In Examples 1 and 5, the ultraviolet absorber is changed to 2-(3-tert-butyl-2-hydroxyl-5-methylphenyl)-5-chloro-2H-benzotriazole (maximum absorption wavelength : 352nm), except that, a plastic lens was obtained in the same manner. Table 1 shows the evaluation results of the obtained lenses.

[Table 1]

The polymerizable monomer (A) and ultraviolet absorber (B) shown in the table|surface are as follows.

(polymerizable monomer)

A1: Bis(isocyanatomethyl)bicyclo[2.2.1]heptane

A2: Pentaerythritol tetrakis (3-mercaptopropionate) ester

A3: 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane

A4: Xylylene Diisocyanate

A5: Bis(2,3-epithiopropyl) disulfide

A6: With 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3, A mixture of 6,9-trithiaundecane and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components

A7: Methyl methacrylate

A8: Ethylene glycol dimethacrylate

(ultraviolet absorber)

B1: 6-(5-Heptylcarbonyloxyethyl-2H-benzotriazol-2-yl)benzo[1,3]dioxol-5-ol

B2: 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chloro-2H-benzotriazole

From the results of the above Examples and Comparative Examples, the following conclusions can be drawn.

Examples 1-8 can all block ultraviolet rays and blue light harmful to the eyes, and effectively suppress the harm of blue light. In contrast, Comparative Examples 1 and 2 have a high light transmittance at a wavelength of 420 nm and a low blue-light blocking rate. From this, it can be seen that when an ultraviolet absorber outside the scope of the present invention is used, the blue-light blocking performance is insufficient.

Claims (5)

1. A composition for optical materials, characterized in that it contains: (A) 100 parts by mass of a polymerizable monomer, and (B) 0.001 to 0.3 parts by mass of an ultraviolet absorber represented by the following formula (1) whose maximum absorption wavelength is 360 nm to less than 380 nm,

Wherein, R1 is an alkyl group with ¹ to 8 carbons, an alkoxy group with 1 to 8 carbons, an alkoxycarbonyl group with 1 to 8 carbons in the alkyl group, a hydroxyalkyl group with 1 to 8 carbons, an alkyl group with 1 to 8 carbons Alkylcarbonyloxyalkyl groups with 1 to 8 carbon atoms, carboxyalkyl groups with 1 to 3 carbon atoms in the alkyl group, or alkoxycarbonylalkyl groups with 2 to 10 carbon atoms in total, ^R2 and ^R3 are crosslinked to form methylenedioxy. 2. The composition for optical materials according to claim 1, wherein the polymerizable monomer (A) contains: At least one polyisocyanate compound selected from bis(isocyanatomethyl)bicyclo[2.2.1]heptane, xylylene diisocyanate, diphenylmethane diisocyanate, and toluene diisocyanate, and At least one polythiol compound selected from pentaerythritol tetrakis(3-mercaptopropionate) and 1,2-bis(2-mercaptoethylthio)-3-mercaptopropane. 3. The composition for optical materials according to claim 1, wherein the polymerizable monomer (A) contains: bis(2,3-epithiopropyl) disulfide, and With 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6, A mixture of 9-trithiaundecane and 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane as main components. 4. An optical material comprising a cured product obtained by polymerizing and curing the composition for optical materials according to any one of claims 1 to 3, wherein the light transmittance at a wavelength of 400 nm is 5% or less, In addition, the light transmittance at a wavelength of 420 nm is 70% or less, and the light blocking rate in the wavelength range of 380 to 500 nm is 35% or more. 5. A plastic lens comprising the optical material according to claim 4.